# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_OF5
_database_code_depnum_ccdc_archive 'CCDC 2052665'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2021-08-10 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
2-(2,4-Dichlorophenyl)-3-hydroxy-4H-chromen-4-one
;
_chemical_formula_moiety         'C15 H8 Cl2 O3'
_chemical_formula_sum            'C15 H8 Cl2 O3'
_chemical_formula_iupac          'C15 H8 Cl2 O3'
_chemical_formula_weight         307.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4976(5)
_cell_length_b                   8.4557(7)
_cell_length_c                   12.4568(11)
_cell_angle_alpha                79.643(4)
_cell_angle_beta                 82.090(4)
_cell_angle_gamma                79.560(3)
_cell_volume                     658.19(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2486
_cell_measurement_theta_min      2.481
_cell_measurement_theta_max      26.500
_cell_measurement_temperature    296(2)
_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_T_max  0.885
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.76
_diffrn_reflns_number            10440
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         27.234
_diffrn_reflns_theta_full        27.234
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             2915
_reflns_number_gt                2486
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         2915
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.1662P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.38762(7) 0.24376(5) 0.37955(4) 0.06056(15) Uani 1 1 d . . . . .
Cl2 Cl 1.14599(10) -0.34169(5) 0.45363(5) 0.0820(2) Uani 1 1 d . . . . .
O1 O 0.84644(15) 0.43156(12) 0.24263(8) 0.0416(2) Uani 1 1 d . . . . .
O2 O 1.27883(16) 0.62331(13) 0.01082(9) 0.0522(3) Uani 1 1 d . . . . .
O3 O 1.37864(16) 0.31149(13) 0.12501(10) 0.0501(3) Uani 1 1 d . . . . .
H3A H 1.452967 0.361829 0.077276 0.075 Uiso 1 1 calc R U . . .
C1 C 0.7972(2) 0.58581(17) 0.18844(11) 0.0381(3) Uani 1 1 d . . . . .
C2 C 0.5955(2) 0.6690(2) 0.21494(14) 0.0498(4) Uani 1 1 d . . . . .
H2 H 0.499398 0.618606 0.265970 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5418(3) 0.8265(2) 0.16415(14) 0.0542(4) Uani 1 1 d . . . . .
H3 H 0.408030 0.883013 0.181280 0.065 Uiso 1 1 calc R U . . .
C4 C 0.6843(3) 0.9032(2) 0.08738(14) 0.0503(4) Uani 1 1 d . . . . .
H4 H 0.646683 1.010798 0.055042 0.060 Uiso 1 1 calc R U . . .
C5 C 0.8801(2) 0.81934(18) 0.05971(13) 0.0437(3) Uani 1 1 d . . . . .
H5 H 0.973352 0.869411 0.006709 0.052 Uiso 1 1 calc R U . . .
C6 C 0.9410(2) 0.65870(17) 0.11065(11) 0.0363(3) Uani 1 1 d . . . . .
C7 C 1.1485(2) 0.56800(17) 0.08285(11) 0.0372(3) Uani 1 1 d . . . . .
C8 C 1.1911(2) 0.40654(17) 0.14512(11) 0.0377(3) Uani 1 1 d . . . . .
C9 C 1.0434(2) 0.34598(17) 0.22121(11) 0.0367(3) Uani 1 1 d . . . . .
C10 C 1.0665(2) 0.17993(17) 0.28374(11) 0.0383(3) Uani 1 1 d . . . . .
C11 C 1.2225(2) 0.11881(18) 0.35352(12) 0.0415(3) Uani 1 1 d . . . . .
C12 C 1.2470(3) -0.04115(19) 0.40674(13) 0.0492(4) Uani 1 1 d . . . . .
H12 H 1.352954 -0.080918 0.452330 0.059 Uiso 1 1 calc R U . . .
C13 C 1.1106(3) -0.13987(18) 0.39050(13) 0.0514(4) Uani 1 1 d . . . . .
C14 C 0.9499(3) -0.0825(2) 0.32566(14) 0.0549(4) Uani 1 1 d . . . . .
H14 H 0.856724 -0.149989 0.317537 0.066 Uiso 1 1 calc R U . . .
C15 C 0.9287(3) 0.0773(2) 0.27251(13) 0.0488(4) Uani 1 1 d . . . . .
H15 H 0.820201 0.116711 0.228459 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7329(16) . ?
Cl2 C13 1.7345(16) . ?
O1 C1 1.3604(17) . ?
O1 C9 1.3684(16) . ?
O2 C7 1.2346(17) . ?
O3 C8 1.3519(16) . ?
O3 H3A 0.8200 . ?
C1 C6 1.3914(19) . ?
C1 C2 1.397(2) . ?
C2 C3 1.373(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.4558(19) . ?
C7 C8 1.4434(19) . ?
C8 C9 1.3544(19) . ?
C9 C10 1.4708(19) . ?
C10 C15 1.391(2) . ?
C10 C11 1.393(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(3) . ?
C14 C15 1.386(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 119.28(11) . . ?
C8 O3 H3A 109.5 . . ?
O1 C1 C6 121.83(12) . . ?
O1 C1 C2 116.98(13) . . ?
C6 C1 C2 121.19(14) . . ?
C3 C2 C1 118.70(15) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.19(14) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.75(15) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.60(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.53(13) . . ?
C1 C6 C7 120.05(12) . . ?
C5 C6 C7 121.42(13) . . ?
O2 C7 C8 122.02(13) . . ?
O2 C7 C6 122.98(13) . . ?
C8 C7 C6 115.00(12) . . ?
O3 C8 C9 119.10(12) . . ?
O3 C8 C7 119.74(12) . . ?
C9 C8 C7 121.12(12) . . ?
C8 C9 O1 122.65(12) . . ?
C8 C9 C10 125.23(12) . . ?
O1 C9 C10 111.97(11) . . ?
C15 C10 C11 117.85(14) . . ?
C15 C10 C9 119.08(13) . . ?
C11 C10 C9 123.07(13) . . ?
C12 C11 C10 121.60(14) . . ?
C12 C11 Cl1 117.88(12) . . ?
C10 C11 Cl1 120.50(11) . . ?
C13 C12 C11 118.47(15) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C14 C13 C12 121.71(15) . . ?
C14 C13 Cl2 119.75(14) . . ?
C12 C13 Cl2 118.54(14) . . ?
C13 C14 C15 119.01(15) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C10 121.29(16) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C6 0.8(2) . . . . ?
C9 O1 C1 C2 -178.76(13) . . . . ?
O1 C1 C2 C3 178.26(14) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C3 C4 C5 C6 -2.1(2) . . . . ?
O1 C1 C6 C5 -178.78(13) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
O1 C1 C6 C7 1.8(2) . . . . ?
C2 C1 C6 C7 -178.64(14) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 -179.65(14) . . . . ?
C1 C6 C7 O2 176.39(14) . . . . ?
C5 C6 C7 O2 -3.0(2) . . . . ?
C1 C6 C7 C8 -2.9(2) . . . . ?
C5 C6 C7 C8 177.71(13) . . . . ?
O2 C7 C8 O3 0.1(2) . . . . ?
C6 C7 C8 O3 179.39(13) . . . . ?
O2 C7 C8 C9 -177.72(15) . . . . ?
C6 C7 C8 C9 1.6(2) . . . . ?
O3 C8 C9 O1 -176.86(13) . . . . ?
C7 C8 C9 O1 0.9(2) . . . . ?
O3 C8 C9 C10 -1.8(2) . . . . ?
C7 C8 C9 C10 175.96(13) . . . . ?
C1 O1 C9 C8 -2.2(2) . . . . ?
C1 O1 C9 C10 -177.83(12) . . . . ?
C8 C9 C10 C15 -118.58(17) . . . . ?
O1 C9 C10 C15 56.90(18) . . . . ?
C8 C9 C10 C11 60.7(2) . . . . ?
O1 C9 C10 C11 -123.82(14) . . . . ?
C15 C10 C11 C12 2.8(2) . . . . ?
C9 C10 C11 C12 -176.48(13) . . . . ?
C15 C10 C11 Cl1 -175.24(11) . . . . ?
C9 C10 C11 Cl1 5.5(2) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
Cl1 C11 C12 C13 177.20(12) . . . . ?
C11 C12 C13 C14 -1.6(2) . . . . ?
C11 C12 C13 Cl2 178.05(11) . . . . ?
C12 C13 C14 C15 2.1(2) . . . . ?
Cl2 C13 C14 C15 -177.58(12) . . . . ?
C13 C14 C15 C10 0.0(2) . . . . ?
C11 C10 C15 C14 -2.3(2) . . . . ?
C9 C10 C15 C14 176.99(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O2 0.82 2.36 2.7715(15) 112.2 . yes
O3 H3A O2 0.82 1.94 2.6820(14) 150.2 2_865 yes
C12 H12 Cl1 0.93 2.87 3.7796(17) 167.4 2_856 yes

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_OF6
_database_code_depnum_ccdc_archive 'CCDC 2052666'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2021-08-10 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
2-(2,3-Dichlorophenyl)-3-hydroxy-4H-chromen-4-one
;
_chemical_formula_moiety         'C15 H8 Cl2 O3'
_chemical_formula_sum            'C15 H8 Cl2 O3'
_chemical_formula_iupac          'C15 H8 Cl2 O3'
_chemical_formula_weight         307.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3596(5)
_cell_length_b                   14.1923(7)
_cell_length_c                   8.1555(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.993(2)
_cell_angle_gamma                90
_cell_volume                     1311.63(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2389
_cell_measurement_theta_min      2.300
_cell_measurement_theta_max      27.535
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'light orange'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.870
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.6
_diffrn_reflns_number            10900
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.870
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_full        27.535
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             3012
_reflns_number_gt                2389
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         3012
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.4899P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.34993(5) 0.73225(4) 0.43542(8) 0.0692(2) Uani 1 1 d . . . . .
Cl2 Cl 0.62005(6) 0.70851(6) 0.51781(10) 0.1020(3) Uani 1 1 d . . . . .
O1 O 0.21129(10) 0.60617(9) 0.04798(13) 0.0429(3) Uani 1 1 d . . . . .
O2 O -0.05540(10) 0.57258(11) 0.35109(16) 0.0560(4) Uani 1 1 d . . . . .
O3 O 0.17569(10) 0.55011(12) 0.47121(15) 0.0586(4) Uani 1 1 d . . . . .
H3A H 0.121566 0.520290 0.507924 0.088 Uiso 1 1 calc R U . . .
C1 C 0.09728(15) 0.62099(12) -0.0120(2) 0.0408(4) Uani 1 1 d . . . . .
C2 C 0.08081(18) 0.64476(14) -0.1779(2) 0.0523(5) Uani 1 1 d . . . . .
H2 H 0.144726 0.649685 -0.242703 0.063 Uiso 1 1 calc R U . . .
C3 C -0.03202(19) 0.66072(14) -0.2431(2) 0.0586(5) Uani 1 1 d . . . . .
H3 H -0.044647 0.676353 -0.353668 0.070 Uiso 1 1 calc R U . . .
C4 C -0.12744(18) 0.65391(15) -0.1468(3) 0.0584(5) Uani 1 1 d . . . . .
H4 H -0.203149 0.665802 -0.193036 0.070 Uiso 1 1 calc R U . . .
C5 C -0.11128(16) 0.62985(13) 0.0156(2) 0.0494(4) Uani 1 1 d . . . . .
H5 H -0.175859 0.625031 0.079248 0.059 Uiso 1 1 calc R U . . .
C6 C 0.00307(14) 0.61241(12) 0.0863(2) 0.0390(4) Uani 1 1 d . . . . .
C7 C 0.02415(14) 0.58487(12) 0.2573(2) 0.0401(4) Uani 1 1 d . . . . .
C8 C 0.14690(14) 0.57241(13) 0.31231(19) 0.0409(4) Uani 1 1 d . . . . .
C9 C 0.23365(14) 0.58435(12) 0.21025(19) 0.0378(4) Uani 1 1 d . . . . .
C10 C 0.36186(14) 0.57371(12) 0.2547(2) 0.0399(4) Uani 1 1 d . . . . .
C11 C 0.42293(15) 0.63822(13) 0.3566(2) 0.0451(4) Uani 1 1 d . . . . .
C12 C 0.54315(16) 0.62777(17) 0.3929(2) 0.0581(5) Uani 1 1 d . . . . .
C13 C 0.60214(18) 0.5525(2) 0.3302(3) 0.0745(7) Uani 1 1 d . . . . .
H13 H 0.682755 0.545302 0.355355 0.089 Uiso 1 1 calc R U . . .
C14 C 0.5422(2) 0.4885(2) 0.2313(3) 0.0762(7) Uani 1 1 d . . . . .
H14 H 0.582279 0.437529 0.189872 0.091 Uiso 1 1 calc R U . . .
C15 C 0.42250(19) 0.49867(15) 0.1921(3) 0.0582(5) Uani 1 1 d . . . . .
H15 H 0.382626 0.455077 0.123558 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.719(2) . ?
Cl2 C12 1.729(2) . ?
O1 C9 1.3656(19) . ?
O1 C1 1.3684(19) . ?
O2 C7 1.236(2) . ?
O3 C8 1.3519(19) . ?
O3 H3A 0.8200 . ?
C1 C6 1.386(2) . ?
C1 C2 1.394(2) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.452(2) . ?
C7 C8 1.445(2) . ?
C8 C9 1.344(2) . ?
C9 C10 1.484(2) . ?
C10 C15 1.385(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.385(2) . ?
C12 C13 1.378(4) . ?
C13 C14 1.365(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 119.26(12) . . ?
C8 O3 H3A 109.5 . . ?
O1 C1 C6 121.95(14) . . ?
O1 C1 C2 116.34(15) . . ?
C6 C1 C2 121.71(16) . . ?
C3 C2 C1 118.34(18) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.03(18) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.58(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.91(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.42(16) . . ?
C1 C6 C7 119.79(14) . . ?
C5 C6 C7 121.79(16) . . ?
O2 C7 C8 121.46(15) . . ?
O2 C7 C6 123.59(15) . . ?
C8 C7 C6 114.94(14) . . ?
C9 C8 O3 118.96(14) . . ?
C9 C8 C7 121.70(15) . . ?
O3 C8 C7 119.32(14) . . ?
C8 C9 O1 122.26(14) . . ?
C8 C9 C10 125.82(14) . . ?
O1 C9 C10 111.91(13) . . ?
C15 C10 C11 119.14(16) . . ?
C15 C10 C9 119.54(17) . . ?
C11 C10 C9 121.32(15) . . ?
C12 C11 C10 120.08(18) . . ?
C12 C11 Cl1 119.81(16) . . ?
C10 C11 Cl1 120.10(13) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 Cl2 119.57(16) . . ?
C11 C12 Cl2 120.35(18) . . ?
C14 C13 C12 120.00(19) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C6 -1.5(2) . . . . ?
C9 O1 C1 C2 178.80(15) . . . . ?
O1 C1 C2 C3 -179.69(17) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
O1 C1 C6 C5 179.30(16) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
O1 C1 C6 C7 -1.4(2) . . . . ?
C2 C1 C6 C7 178.25(17) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -178.77(17) . . . . ?
C1 C6 C7 O2 -177.41(17) . . . . ?
C5 C6 C7 O2 1.9(3) . . . . ?
C1 C6 C7 C8 2.6(2) . . . . ?
C5 C6 C7 C8 -178.18(16) . . . . ?
O2 C7 C8 C9 179.02(17) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
O2 C7 C8 O3 -2.4(3) . . . . ?
C6 C7 C8 O3 177.64(16) . . . . ?
O3 C8 C9 O1 179.45(16) . . . . ?
C7 C8 C9 O1 -2.0(3) . . . . ?
O3 C8 C9 C10 1.1(3) . . . . ?
C7 C8 C9 C10 179.70(16) . . . . ?
C1 O1 C9 C8 3.2(2) . . . . ?
C1 O1 C9 C10 -178.20(14) . . . . ?
C8 C9 C10 C15 110.6(2) . . . . ?
O1 C9 C10 C15 -67.9(2) . . . . ?
C8 C9 C10 C11 -70.2(2) . . . . ?
O1 C9 C10 C11 111.29(17) . . . . ?
C15 C10 C11 C12 0.8(3) . . . . ?
C9 C10 C11 C12 -178.47(16) . . . . ?
C15 C10 C11 Cl1 179.76(14) . . . . ?
C9 C10 C11 Cl1 0.5(2) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
Cl1 C11 C12 C13 179.94(16) . . . . ?
C10 C11 C12 Cl2 179.28(13) . . . . ?
Cl1 C11 C12 Cl2 0.3(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
Cl2 C12 C13 C14 -179.88(18) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C9 C10 C15 C14 179.37(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O2 0.82 1.94 2.6973(18) 154.2 3_566 yes
C13 H13 O3 0.93 2.47 3.247(2) 141.1 3_666 yes

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.042

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_OF7uom
_database_code_depnum_ccdc_archive 'CCDC 2052667'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2021-08-10 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
2-(2,6-Dichlorophenyl)-3-hydroxy-4H-chromen-4-one
;
_chemical_formula_moiety         'C15 H8 Cl2 O3'
_chemical_formula_sum            'C15 H8 Cl2 O3'
_chemical_formula_iupac          'C15 H8 Cl2 O3'
_chemical_formula_weight         307.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.6464(5)
_cell_length_b                   11.3272(7)
_cell_length_c                   15.5325(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.017(3)
_cell_angle_gamma                90
_cell_volume                     1320.51(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2348
_cell_measurement_theta_min      2.240
_cell_measurement_theta_max      27.532
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.875
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.6
_diffrn_reflns_number            10910
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.240
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        27.532
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             3023
_reflns_number_gt                2348
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_number_reflns         3023
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.4020P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.23403(8) 0.34277(5) 0.24500(3) 0.06325(18) Uani 1 1 d . . . . .
Cl2 Cl 0.31804(8) 0.39710(6) -0.08919(4) 0.06893(19) Uani 1 1 d . . . . .
O1 O 0.51771(14) 0.24933(10) 0.11744(8) 0.0425(3) Uani 1 1 d . . . . .
O2 O 0.21166(16) -0.04276(10) 0.04758(8) 0.0460(3) Uani 1 1 d . . . . .
O3 O 0.06344(15) 0.18070(10) 0.02394(10) 0.0538(4) Uani 1 1 d . . . . .
H3A H 0.015067 0.117044 0.010127 0.081 Uiso 1 1 calc R U . . .
C1 C 0.5931(2) 0.13958(15) 0.13128(10) 0.0383(4) Uani 1 1 d . . . . .
C2 C 0.7732(2) 0.13727(18) 0.16931(13) 0.0516(5) Uani 1 1 d . . . . .
H2 H 0.836249 0.206898 0.184029 0.062 Uiso 1 1 calc R U . . .
C3 C 0.8554(3) 0.0293(2) 0.18456(13) 0.0587(5) Uani 1 1 d . . . . .
H3 H 0.975975 0.025962 0.209475 0.070 Uiso 1 1 calc R U . . .
C4 C 0.7608(3) -0.07528(19) 0.16325(13) 0.0555(5) Uani 1 1 d . . . . .
H4 H 0.818448 -0.147543 0.174389 0.067 Uiso 1 1 calc R U . . .
C5 C 0.5838(2) -0.07208(16) 0.12607(11) 0.0449(4) Uani 1 1 d . . . . .
H5 H 0.521526 -0.142136 0.111839 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4955(2) 0.03676(14) 0.10928(10) 0.0358(3) Uani 1 1 d . . . . .
C7 C 0.3075(2) 0.04409(13) 0.06928(10) 0.0350(3) Uani 1 1 d . . . . .
C8 C 0.2369(2) 0.16307(14) 0.05757(11) 0.0362(3) Uani 1 1 d . . . . .
C9 C 0.3410(2) 0.25776(14) 0.08174(10) 0.0364(3) Uani 1 1 d . . . . .
C10 C 0.2775(2) 0.38145(14) 0.07911(11) 0.0384(4) Uani 1 1 d . . . . .
C11 C 0.2283(2) 0.43029(15) 0.15288(12) 0.0447(4) Uani 1 1 d . . . . .
C12 C 0.1745(3) 0.54648(17) 0.15567(14) 0.0591(5) Uani 1 1 d . . . . .
H12 H 0.142777 0.577224 0.206046 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1689(3) 0.61537(18) 0.08286(16) 0.0659(6) Uani 1 1 d . . . . .
H13 H 0.134967 0.694062 0.084397 0.079 Uiso 1 1 calc R U . . .
C14 C 0.2122(3) 0.57080(18) 0.00797(15) 0.0620(6) Uani 1 1 d . . . . .
H14 H 0.206049 0.618297 -0.041355 0.074 Uiso 1 1 calc R U . . .
C15 C 0.2657(2) 0.45348(16) 0.00630(12) 0.0470(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7344(19) . ?
Cl2 C15 1.731(2) . ?
O1 C9 1.3625(19) . ?
O1 C1 1.370(2) . ?
O2 C7 1.2343(19) . ?
O3 C8 1.3446(19) . ?
O3 H3A 0.8200 . ?
C1 C6 1.390(2) . ?
C1 C2 1.391(2) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.455(2) . ?
C7 C8 1.450(2) . ?
C8 C9 1.345(2) . ?
C9 C10 1.481(2) . ?
C10 C15 1.383(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.382(3) . ?
C12 C13 1.368(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 118.85(12) . . ?
C8 O3 H3A 109.5 . . ?
O1 C1 C6 122.10(14) . . ?
O1 C1 C2 115.88(15) . . ?
C6 C1 C2 122.02(16) . . ?
C3 C2 C1 118.23(18) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.03(18) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.30(18) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.22(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.20(15) . . ?
C1 C6 C7 119.83(14) . . ?
C5 C6 C7 121.97(15) . . ?
O2 C7 C8 121.30(14) . . ?
O2 C7 C6 123.87(14) . . ?
C8 C7 C6 114.82(14) . . ?
O3 C8 C9 118.48(14) . . ?
O3 C8 C7 120.15(14) . . ?
C9 C8 C7 121.34(14) . . ?
C8 C9 O1 123.04(14) . . ?
C8 C9 C10 124.98(14) . . ?
O1 C9 C10 111.84(13) . . ?
C15 C10 C11 117.04(16) . . ?
C15 C10 C9 123.37(16) . . ?
C11 C10 C9 119.59(15) . . ?
C12 C11 C10 122.33(18) . . ?
C12 C11 Cl1 118.64(16) . . ?
C10 C11 Cl1 119.03(13) . . ?
C13 C12 C11 118.7(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 121.27(19) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C10 C15 C14 121.40(19) . . ?
C10 C15 Cl2 119.58(14) . . ?
C14 C15 Cl2 119.02(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C6 0.6(2) . . . . ?
C9 O1 C1 C2 -178.91(15) . . . . ?
O1 C1 C2 C3 -179.95(17) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
O1 C1 C6 C5 -179.82(15) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
O1 C1 C6 C7 0.7(2) . . . . ?
C2 C1 C6 C7 -179.76(15) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 C7 179.60(16) . . . . ?
C1 C6 C7 O2 179.77(15) . . . . ?
C5 C6 C7 O2 0.3(2) . . . . ?
C1 C6 C7 C8 -1.3(2) . . . . ?
C5 C6 C7 C8 179.28(15) . . . . ?
O2 C7 C8 O3 1.2(2) . . . . ?
C6 C7 C8 O3 -177.79(14) . . . . ?
O2 C7 C8 C9 179.55(16) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
O3 C8 C9 O1 179.18(14) . . . . ?
C7 C8 C9 O1 0.8(3) . . . . ?
O3 C8 C9 C10 3.8(3) . . . . ?
C7 C8 C9 C10 -174.64(15) . . . . ?
C1 O1 C9 C8 -1.4(2) . . . . ?
C1 O1 C9 C10 174.54(14) . . . . ?
C8 C9 C10 C15 -88.7(2) . . . . ?
O1 C9 C10 C15 95.46(18) . . . . ?
C8 C9 C10 C11 92.1(2) . . . . ?
O1 C9 C10 C11 -83.77(18) . . . . ?
C15 C10 C11 C12 -1.8(3) . . . . ?
C9 C10 C11 C12 177.45(16) . . . . ?
C15 C10 C11 Cl1 178.12(12) . . . . ?
C9 C10 C11 Cl1 -2.6(2) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
Cl1 C11 C12 C13 -179.62(15) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C11 C10 C15 C14 1.9(2) . . . . ?
C9 C10 C15 C14 -177.30(17) . . . . ?
C11 C10 C15 Cl2 -177.93(13) . . . . ?
C9 C10 C15 Cl2 2.8(2) . . . . ?
C13 C14 C15 C10 -0.6(3) . . . . ?
C13 C14 C15 Cl2 179.29(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O2 0.82 2.35 2.7690(17) 112.1 . yes
O3 H3A O2 0.82 1.98 2.6846(16) 143.5 3 yes

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.043

